R59022
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561705

CAS#: 93076-89-2

Description: R59022 is a DGKalpha inhibitor and serotonin receptor antagonist.


Chemical Structure

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R59022
CAS# 93076-89-2

Theoretical Analysis

MedKoo Cat#: 561705
Name: R59022
CAS#: 93076-89-2
Chemical Formula: C27H26FN3OS
Exact Mass: 459.1781
Molecular Weight: 459.58
Elemental Analysis: C, 70.56; H, 5.70; F, 4.13; N, 9.14; O, 3.48; S, 6.98

Price and Availability

Size Price Availability Quantity
5.0mg USD 225.0 2 weeks
10.0mg USD 380.0 2 weeks
50.0mg USD 1000.0 2 weeks
Bulk inquiry

Synonym: R59022; R-59022; R 59022;

IUPAC/Chemical Name: 6-[2-[4-[(4-Fluorophenyl)-phenylmethylidene]piperidin-1-yl]ethyl]-7-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one

InChi Key: MFVJXLPANKSLLD-UHFFFAOYSA-N

InChi Code: InChI=1S/C27H26FN3OS/c1-19-24(26(32)31-17-18-33-27(31)29-19)13-16-30-14-11-22(12-15-30)25(20-5-3-2-4-6-20)21-7-9-23(28)10-8-21/h2-10,17-18H,11-16H2,1H3

SMILES Code: O=C1C(CCN2CC/C(CC2)=C(C3=CC=C(F)C=C3)\C4=CC=CC=C4)=C(C)N=C5N1C=CS5

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 459.58 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: McCloud RL, Franks CE, Campbell ST, Purow BW, Harris TE, Hsu KL. Deconstructing Lipid Kinase Inhibitors by Chemical Proteomics. Biochemistry. 2017 Nov 22. doi: 10.1021/acs.biochem.7b00962. [Epub ahead of print] PubMed PMID: 29155586.

2: Boroda S, Niccum M, Raje V, Purow BW, Harris TE. Dual activities of ritanserin and R59022 as DGKα inhibitors and serotonin receptor antagonists. Biochem Pharmacol. 2016 Oct 27. pii: S0006-2952(16)30380-X. doi: 10.1016/j.bcp.2016.10.011. [Epub ahead of print] PubMed PMID: 27989726.

3: Boroda S, Niccum M, Raje V, Purow BW, Harris TE. Dual activities of ritanserin and R59022 as DGKα inhibitors and serotonin receptor antagonists. Biochem Pharmacol. 2017 Jan 1;123:29-39. doi: 10.1016/j.bcp.2016.10.011. Epub 2016 Oct 28. PubMed PMID: 27974147; PubMed Central PMCID: PMC5164959.

4: Ruffo E, Malacarne V, Larsen SE, Das R, Patrussi L, Wülfing C, Biskup C, Kapnick SM, Verbist K, Tedrick P, Schwartzberg PL, Baldari CT, Rubio I, Nichols KE, Snow AL, Baldanzi G, Graziani A. Inhibition of diacylglycerol kinase α restores restimulation-induced cell death and reduces immunopathology in XLP-1. Sci Transl Med. 2016 Jan 13;8(321):321ra7. doi: 10.1126/scitranslmed.aad1565. PubMed PMID: 26764158; PubMed Central PMCID: PMC4918505.

5: Sovadinova I, Babica P, Böke H, Kumar E, Wilke A, Park JS, Trosko JE, Upham BL. Phosphatidylcholine Specific PLC-Induced Dysregulation of Gap Junctions, a Robust Cellular Response to Environmental Toxicants, and Prevention by Resveratrol in a Rat Liver Cell Model. PLoS One. 2015 May 29;10(5):e0124454. doi: 10.1371/journal.pone.0124454. eCollection 2015. Erratum in: PLoS One. 2015;10(9):e0137599. PubMed PMID: 26023933; PubMed Central PMCID: PMC4449167.

6: Natalini PM, Mateos MV, Ilincheta de Boschero MG, Giusto NM. A novel light-dependent activation of DAGK and PKC in bovine photoreceptor nuclei. Exp Eye Res. 2014 Aug;125:142-55. doi: 10.1016/j.exer.2014.06.007. Epub 2014 Jun 17. PubMed PMID: 24950064.

7: Catacuzzeno L, Michelucci A, Sforna L, Aiello F, Sciaccaluga M, Fioretti B, Castigli E, Franciolini F. Identification of key signaling molecules involved in the activation of the swelling-activated chloride current in human glioblastoma cells. J Membr Biol. 2014 Jan;247(1):45-55. doi: 10.1007/s00232-013-9609-9. Epub 2013 Nov 16. PubMed PMID: 24240542.

8: Djafi N, Vergnolle C, Cantrel C, Wietrzyñski W, Delage E, Cochet F, Puyaubert J, Soubigou-Taconnat L, Gey D, Collin S, Balzergue S, Zachowski A, Ruelland E. The Arabidopsis DREB2 genetic pathway is constitutively repressed by basal phosphoinositide-dependent phospholipase C coupled to diacylglycerol kinase. Front Plant Sci. 2013 Aug 8;4:307. doi: 10.3389/fpls.2013.00307. eCollection 2013. PubMed PMID: 23964284; PubMed Central PMCID: PMC3737466.

9: Sato M, Liu K, Sasaki S, Kunii N, Sakai H, Mizuno H, Saga H, Sakane F. Evaluations of the selectivities of the diacylglycerol kinase inhibitors R59022 and R59949 among diacylglycerol kinase isozymes using a new non-radioactive assay method. Pharmacology. 2013;92(1-2):99-107. doi: 10.1159/000351849. Epub 2013 Aug 16. PubMed PMID: 23949095.

10: Natalini PM, Zulian SE, Ilincheta de Boschero MG, Giusto NM. Diacylglycerol kinase epsilon in bovine and rat photoreceptor cells. Light-dependent distribution in photoreceptor cells. Exp Eye Res. 2013 Jul;112:139-50. doi: 10.1016/j.exer.2013.04.012. Epub 2013 Apr 19. PubMed PMID: 23608524.

11: Dominguez CL, Floyd DH, Xiao A, Mullins GR, Kefas BA, Xin W, Yacur MN, Abounader R, Lee JK, Wilson GM, Harris TE, Purow BW. Diacylglycerol kinase α is a critical signaling node and novel therapeutic target in glioblastoma and other cancers. Cancer Discov. 2013 Jul;3(7):782-97. doi: 10.1158/2159-8290.CD-12-0215. Epub 2013 Apr 4. PubMed PMID: 23558954; PubMed Central PMCID: PMC3710531.

12: Tu-Sekine B, Goldschmidt H, Petro E, Raben DM. Diacylglycerol kinase θ: regulation and stability. Adv Biol Regul. 2013 Jan;53(1):118-26. doi: 10.1016/j.jbior.2012.09.007. Epub 2012 Sep 20. PubMed PMID: 23266086; PubMed Central PMCID: PMC3992713.

13: Martinez K, Shyamasundar S, Kennedy A, Chuang CC, Marsh A, Kincaid J, Reid T, McIntosh M. Diacylglycerol kinase inhibitor R59022 attenuates conjugated linoleic acid-mediated inflammation in human adipocytes. J Lipid Res. 2013 Mar;54(3):662-70. doi: 10.1194/jlr.M031211. Epub 2012 Dec 22. PubMed PMID: 23264678; PubMed Central PMCID: PMC3617941.

14: Nakano T, Hozumi Y, Goto K, Wakabayashi I. Involvement of diacylglycerol kinase γ in modulation of iNOS synthesis in Golgi apparatus of vascular endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2012 Aug;385(8):787-95. doi: 10.1007/s00210-012-0760-0. Epub 2012 May 25. PubMed PMID: 22627682.

15: Holden NJ, Savage CO, Young SP, Wakelam MJ, Harper L, Williams JM. A dual role for diacylglycerol kinase generated phosphatidic acid in autoantibody-induced neutrophil exocytosis. Mol Med. 2011;17(11-12):1242-52. doi: 10.2119/molmed.2011.00028. Epub 2011 Aug 8. PubMed PMID: 21833457; PubMed Central PMCID: PMC3321818.

16: Takita T, Konuma T, Hanazato M, Inoue H. Diacylglycerol kinase inhibitor R59022-induced autophagy and apoptosis in the neuronal cell line NG108-15. Arch Biochem Biophys. 2011 May 15;509(2):197-201. doi: 10.1016/j.abb.2011.02.007. Epub 2011 Feb 19. PubMed PMID: 21338572.

17: Shibata Y, Kawada-Matsuo M, Shirai Y, Saito N, Li D, Yamashita Y. Streptococcus mutans diacylglycerol kinase homologue: a potential target for anti-caries chemotherapy. J Med Microbiol. 2011 May;60(Pt 5):625-30. doi: 10.1099/jmm.0.026070-0. Epub 2011 Feb 11. PubMed PMID: 21317193.

18: Kamio N, Akifusa S, Yamashita Y. Diacylglycerol kinase alpha regulates globular adiponectin-induced reactive oxygen species. Free Radic Res. 2011 Mar;45(3):336-41. doi: 10.3109/10715762.2010.532495. Epub 2010 Nov 1. PubMed PMID: 21034360.

19: Kito Y, Suzuki H. Properties of Rikkunshi-to (TJ-43)-induced relaxation of rat gastric fundus smooth muscles. Am J Physiol Gastrointest Liver Physiol. 2010 May;298(5):G755-63. doi: 10.1152/ajpgi.00333.2009. Epub 2010 Feb 18. PubMed PMID: 20167876.

20: Zulian SE, de Boschero MG, Giusto NM. Insulin action on polyunsaturated phosphatidic acid formation in rat brain: an "in vitro" model with synaptic endings from cerebral cortex and hippocampus. Neurochem Res. 2009 Jul;34(7):1236-48. doi: 10.1007/s11064-008-9901-8. Epub 2009 Jan 7. PubMed PMID: 19130221.

R59022

5.0mg / USD 225.0